Journal article

Asymmetric synthesis of nortropanes via Rh-catalyzed allylic arylation

Abstract:: Tropane derivatives are extensively used in medicine, but catalytic asymmetric methods for their synthesis are underexplored. Here we report Rh-catalyzed asymmetric Suzuki-Miyaura type cross-coupling reactions between a racemic N-Bocnortropane-derived allylic chloride and (hetero-)aryl-boronic esters. The reaction proceeds via an unexpected kinetic resolution, and the resolved enantiopure allyl chloride can undergo highly enantiospecific reactions with N, O, and S-containing nucleophiles. The method was applied in a highly stereoselective formal synthesis of YZJ-1139(1), a potential insomnia treatment that recently completed Phase II clinical trials. Our report represents an asymmetric catalytic method for the synthesis of YZJ-1139(1) and related compounds.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Zhang, Y., Goetzke, F., Christensen, K., & Fletcher, S. P. (2022). Asymmetric synthesis of nortropanes via Rh-catalyzed allylic arylation. ACS Catalysis, 12(15), 8995–9002.

MLA Style

Zhang, Y., et al. “Asymmetric Synthesis of Nortropanes via Rh-Catalyzed Allylic Arylation.” ACS Catalysis, vol. 12, no. 15, American Chemical Society, 2022, pp. 8995–9002.

Chicago Style

Zhang, Y, F Goetzke, K Christensen, and SP Fletcher. 2022. “Asymmetric Synthesis of Nortropanes via Rh-Catalyzed Allylic Arylation.” ACS Catalysis 12 (15): 8995–9002.
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Files:: Zhang_et_al_2022_asymmetric_synthesis_of.pdf

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Publisher copy:: 10.1021/acscatal.2c02259

Authors

+ Zhang, Y More by this author

Role:: Author

+ Goetzke, F More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Role:: Author

+ Christensen, K More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Role:: Author

+ Fletcher, SP More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Role:: Author

+ Engineering and Physical Sciences Research Council More from this funder

Grant:: EP/N022246/1

Publisher:: American Chemical Society
Journal:: ACS Catalysis More from this journal
Volume:: 12
Issue:: 15
Pages:: 8995–9002
Publication date:: 2022-07-12
Acceptance date:: 2022-06-28
DOI:: 10.1021/acscatal.2c02259
EISSN:: 2155-5435

Language:: English
Keywords:: FFR
Pubs id:: 1266517
Local pid:: pubs:1266517
Deposit date:: 2022-07-04

Terms of use

Copyright holder:: Zhang et al
Copyright date:: 2022
Rights statement:: © 2022 The Authors. Published by American Chemical Society. This paper is made open access via creative commons licensing (https://creativecommons.org/licenses/by/4.0/).

Licence:: CC Attribution (CC BY)

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